How to Have a Perfect Multi-Generation Family Vacation

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It probably isn’t the most onerous element of being a member of the sandwich generation, but it’s not easy to be mid-level on the family tree when you’re planning a multi-gen family vacation. Not to diminish my lovely parents’ decades of wisdom and experience, but the needs posed by my four children and my seventy-something parents are not dissimilar: Sleeping arrangements require careful consideration, long waits of any variety are not generally appreciated, and the meal schedule should not be left up to happenstance. Of course, these are concerns that apply to all of us. But there is something admirably stripped-back and unaccommodating in the expectations of the young and not-so-young.

As the lynchpin of my family’s recent endeavor to vacation with three generations, I came up against the fundamental challenge: The needs may not be dissimilar, but the aspirations certainly are. If you ask my children for their ideal vacation scenario, they would probably offer you something like: arcade, candy, ice cream, water slide, arcade, kayak, pool, more ice cream. For my parents (and quite frankly me), it might be something more like: beach, reading, ocean, reading, wine, reading, dinner. Not a ton of overlap.

And yet, I set out to make the two paths converge, not just for the extra hands and help with my kids, but because time is fleeting and there is something magical about plucking my urban creatures out of their urban jungles and shocking them with the glaring optics of white-hot sand and aqua waters. Every trip I’ve ever taken with my children—from a villa in Umbria to a motel on the Jersey Shore—has been embedded in their little minds in some indelible way. (Thank you Asbury Park boardwalk for searing the bright lights of the arcade deep in their impressionable minds.) “When are we going to Miami,” they started asking me around Christmas last year, recalling the mid-winter trip we had taken to visit my college roommate the year before. “We don’t, like, get to go to Miami every year,” I explained to them. “Yeah, but when are we going back?” they intoned.

And I’m not alone in thinking that memory-making is all the sweeter when shared up and down the family tree. Declining Covid concerns may play a part in the increasing willingness of older generations to travel; cost recently overtook Covid as the prohibitive factor for mature travelers in 2023 according to the AARP. But there’s also a more generalized shift toward multi-gen travel: The travel company Virtuoso found that 44 percent of the people it recently surveyed planned to travel with children under 18 and 20 percent planned to travel with extended families. “Togetherness was lost during the pandemic,” says Misty Belles, VP of global public relations for Virtuoso, “and people are still making up for the lack of time spent with loved ones.”

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